Thursday, July 23, 2009

First it was “Keep It Simple, Stupid.” Then it was, “It’s the Software, Stupid.” Now I’m thinking “It’s the Data Stupid.”

There are two kinds of people in the world: A) Those who think email is the killer app; and B) Those who don’t. I’m a type A person (in more ways than one, but I digress.) And mostly those whose opinions I respect believe mail is the killer app. My wife has a couple hundred Megs of Outlook email, contact and calendar data squirreled away on her PC. Me? It’s about a Gig. We need to get that into the Mac in a way that it continues to make sense. But the Mac doesn’t speak Outlook. And Outlook doesn’t speak Mac.

We had a choice, move the data to Microsoft Entourage (an Outlook clone) on the Mac or move the data to the Mac’s native mail, iCal, and Address Book applications. For reasons that revolve around synching with our iPhones, we chose to use Mac’s native applications. They are not as capable as Entourage, but they look to be “plenty good enough.” (Check out “The Rest of the Story” to see what pushed us over the edge.)

And to get the data into the native apps, we followed Apple’s recommendation and bought a copy of Little Machine’s Outlook to Mac (O2M) for short. For $10, how wrong could we go?

Pretty wrong as it turns out! Trouble is, out of the box, in its standard configuration … it doesn’t work. It fails to export more than one contact. It destroys calendar data. And exporting email folders is frustrating on a nuclear scale. ARGH! What to do?

Calling Apple, we worked over the issue for a few hours and developed some work-arounds. Mail folders – decide that “frustration is the new bliss” and suck it up. For calendar – export to an ics format directly from Outlook. Easier than O2M, actually. For contacts – using O2M and exporting to a previous vCard format works great. Then use native app “import” functions as is.

It worked!!! We’re done on Nancy’s iMac. My Mac Pro is next. I’m confident it will work there two and more simply - now that I know how.

How are iTunes; Mac mail, iCal, & Address Book; and Entourage related? You’ll have to read The Rest of the Story.

Our goal is to synch calendar and contact info between our iPhones and the computer.

This is about moving parts.

It is true that a 4-engine aircraft, such as a Boeing 747, has more engine failures than a two-enginee aircraft, such as a Boeing 777. More moving parts = greater number of failures.

On the PC, iTunes is the synch agent that keeps Outlook calendar and contacts in synch with the iPhone. On the Mac, iTunes synchs the phone with the native apps. And Entourage synchs with the native apps. Sounds like were adding engines! KISS, remember? If we can live with the functionality of the native apps, it makes thing simpler – fewer moving parts. Fewer things to go wrong.

We’re going to try.